3-Pyridinemethanamine → HCID 178422563, compound

HRID 580867Notes

Reaction equation

HRID 580867 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8](=S)[NH:7][C:6]=2[CH:17]=1.[NH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>C(OCCO)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 54258643HCID 54258643, compound

Product 1

HCID 178422563HCID 178422563, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.32 g (1.3 mmol) of 8-methyl-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione (Hunziker F., et al., Helv. Chim. Acta, 50:1588 (1967)) in 10 mL 2-ethoxyethanol was treated with 0.3 mL (2.9 mmol) of 3-(aminomethyl)pyridine and heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed two times with H2O, then saturated NaHCO3 solution and saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Recrystallization from EtOAc/hexane gave 0.2 g (50% yield) of the pure product as a light yellow solid, mp 186-187° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =315.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. washwashed two times with H2O
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. waitleft the crude product
  7. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-d7e27e65fcef4e918c112d6ccc7582b8
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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